Tim Cook Joined a Near-Bankrupt Apple in 1998, Calling It the ‘Chance of a Lifetime’ —Now It’s a $3.3 Trillion Giant, But Its AI Flop Has Critics Calling for His Resignation

In the late 1990s, Tim Cook was comfortably seated in a stable, well-paying role at Compaq Computer Corporation, following a 12-year tenure at International Business Machines (IBM) that had provided him with predictability, structure, and status. But in 1998, he made a decision that many close to him likely saw as reckless: He left the comfort of his corporate career to join a less well-known startup bleeding money, lacking direction, and teetering on the edge of bankruptcy. The company in question? Apple (AAPL). 

Tim Cook’s path from a steady career at IBM to the high-wire act of leading Apple through its most innovative — and controversial — era is a case study in modern leadership. Cook, once known for his quiet operational genius behind the scenes, now finds himself at the center of intense public scrutiny as Apple weathers a string of stumbles in the AI age.

The Leap from Comfort to Chaos

In 1998, when Cook left a prestigious post at Compaq, Apple was bleeding cash, saddled with an unfocused product line and dwindling consumer confidence. But for Cook, the draw wasn’t financial; it was the potential. The opportunity to work alongside Steve Jobs and help resurrect a dying icon was, as he later described, “the chance of a lifetime.”

Cook quickly proved indispensable. While Jobs remained the face of Apple’s creative revolution, it was Cook who overhauled the company’s supply chain, slashing costs and accelerating time to market. Apple’s recovery — and its rise to global dominance — was fueled as much by operational precision as by visionary design.

By the time Jobs stepped down in 2011, Cook was the obvious successor. Under his leadership, Apple transitioned from a scrappy innovator to the world’s most valuable company. The iPhone exploded globally, Services became a revenue juggernaut, and new categories like the Apple Watch and AirPods became cultural staples. The company’s market capitalization soared from $364 billion in 2011 to $3.294 trillion based on today’s price.

The Long Shadow of Innovation

But with success came new expectations. In recent years, Cook has been lauded less for creating paradigm-shifting products and more for steering Apple with Wall Street-friendly discipline. As the iPhone matured and hardware growth slowed, critics began asking if Apple had lost its edge.

2024 was a turning point. A slate of underwhelming product updates and bold bets that didn’t land as expected cast doubt on Cook’s legacy — and future.

Chief among the concerns: Apple Intelligence, the company’s long-awaited generative AI initiative. Touted as Apple’s answer to OpenAI, Google Gemini, and Microsoft Copilot, it promised seamless integration into users’ digital lives. But the actual rollout was fraught with missteps.

A highly publicized ad campaign showcased features that didn’t exist. Users were promised an assistant that could recall past interactions and summarize content across apps — only to discover the final product fell short. Analysts, already wary of the hype surrounding AI, accused Apple of overpromising and underdelivering. Developer backlash and tepid adoption followed.

And while the Apple Vision Pro, a high-end mixed reality headset, was praised for its design, its $3,500 price tag and limited software support turned it into more of a niche experiment than a mass-market revolution. Early sales have been modest, and enthusiasm has waned. The Vision Pro is now largely considered a complete flop, with production reportedly shuttered late last year. 

The final blow to Apple’s sheen in 2024 came when the company canceled its long-rumored electric car project, a decade-long investment that never bore fruit.

Successes Amid Setbacks

Despite the turbulence, Apple hasn’t lost its footing entirely. The iPhone 16 series, while not a revolutionary leap, delivered modest gains in speed, camera quality, and battery life. AirPods Pro 3 continued to dominate the wireless audio market, and Apple Services—including iCloud+, Apple TV+, and Fitness+ — have kept revenue flowing even as hardware sales slowed.

Meanwhile, the Apple Watch Ultra 2 proved a bright spot, appealing to athletes and outdoor enthusiasts with new health tracking and satellite SOS features. Even the Vision Pro, for all its flaws, opened the door to Apple’s future in spatial computing and helped push advancements in chip design and display tech.

And the company remains a cash machine. Cook’s strategy of massive stock buybacks and disciplined financial management has kept investors mostly content, even as innovation wobbles.

The Call for Cook to Step Down

But whispers have turned to shouts. As Apple Intelligence continues to lag behind competitors, and Apple’s aura of infallibility cracks, some are calling for new leadership. Cook, now 64, has acknowledged retirement questions are becoming more frequent. Still, insiders report he has no immediate plans to step down, with a potential timeline stretching another three years.

Apple has groomed internal candidates, with Jeff Williams, Apple’s COO, and John Ternus, head of hardware engineering, often floated as potential successors. Cook has emphasized that he wants the next CEO to be chosen from within — maintaining Apple’s continuity and culture.

But while succession planning looms, Cook’s defenders argue that ousting him now would be shortsighted. Apple’s long-term bets — including AI, health tech, and AR — require patient capital and steady leadership. Cook’s critics often forget that his first few years as CEO were met with similar doubts, only to be followed by explosive growth. 

It’s easy to forget that Apple stock is still up over 1500% since Cook took the reins in 2011, and that’s not accounting for dividends. And even amid the “lackluster” performance of Apple, currently up nearly 28% over the previous 12 months, a new CEO poses a whole new set of risks. Managing a $3.3 trillion company isn’t something just anyone can walk into, and arguably, it’s not something anyone else in the world is qualified to do. Apple still maintains a respectable lead ahead of the #2 company, a $2.93 trillion Nvidia. 

Legacy in Progress

Ultimately, Cook’s story is one of transformation. He took a company built on charismatic vision and reshaped it into a fortress of operational excellence. He may not be a "product person" in the mold of Jobs, but he has redefined what it means to lead Apple in the post-Jobs era.

The road ahead is uncertain. Apple faces intensifying competition, shifting consumer expectations, and technological upheaval. But if Cook has proven anything, it’s that he’s more than just a caretaker CEO. He’s a builder of systems, a master of scale, and a strategist willing to play the long game.

Whether he stays another three years or steps down tomorrow, Cook has already secured a legacy few in Silicon Valley, or anywhere, can match. The only question is whether Apple, under his final chapters, can still surprise the world the way it once did.